During a summer break from Connecticut College in 1991, Armstrong and a couple of his buddies learned through a friend's father that a nearby strawberry farm was in bankruptcy. Armstrong convinced a bank to let him and his pals run the farm over the summer.

At first, Armstrong hired a few workers to pick all the ripe strawberries so he could sell them. But then he had an idea. What if he just put out a sign out front that said 'you pick strawberries’ and then charged people who stopped by? It worked. People drove up and paid him to do all the work.

"We made thousands of dollars," Armstrong says. "At the time it was a lot."

Back at school, Armstrong majored in economics and sociology. He was also a star athlete, rowing for the first-boat heavyweight crew and playing lacrosse.

Socially, Armstrong was the well-liked popular kid who, as a sophomore, hung out with seniors. One of those seniors, Jen Schumacher Harper, says Armstrong was "goofy and fun and the life of the party."

That's the kind of nice thing people throughout Armstrong's life say about him. Even his detractors say you can't be in a room with him and not warm up to him. He's got that Bill Clinton thing.

Maybe it's Armstrong's height. Maybe it's his skill with eye contact. Maybe it's that Armstrong is a big, handsome guy with severe cheekbones and dark hair who looks like a Bond movie villain but turns out to be nice when he starts talking. It makes you open up to him immediately and want to play on his team.

After college, Armstrong moved to Boston and worked in finance. He hated it and quit. The people were not his kind of people, he says.

To figure out what to do with his life, Armstrong started cold-calling prominent business executives. They wouldn't take his calls. Finally, an executive assistant took pity on him and gave him a clue: “The only way you’ll get through is if you’re a reporter, or if you know someone they know.”

So Armstrong started a small newspaper called BIB, for "Beginnings in Boston." Later Armstrong folded that paper into a bigger one, which he sold.

By the summer of 1995, Armstrong was 24 and ready to work for a major company. He'd been to a presentation on the Web browser at MIT and had decided the Internet was the future. Then he sold ads for a small Web publisher in Boston. But this was still the minor leagues. So, Armstrong moved to Seattle and found a job selling advertising at a company called Starwave, which was owned by Microsoft co-founder Paul Allen. Starwave built and monetized websites for established brands such as Outside magazine, ESPN, and the NFL.

Armstrong's job was to sell ads for Starwave. Right away he was very good at it.

Says a former colleague: "At the risk of offending all the other people who were working as his peers, he was the star. He was the guy who stood out from the beginning as having the focus, the intelligence, the charm, and the drive to make things happen. He was the kid that everyone loved. Everyone had their eye on him and everyone said, ‘I want him to be part of my team.’"

Another reason Armstrong did well at Starwave was that he was a killer athlete. At Starwave, that mattered. The company ran ESPN.com, NFL.com, NASCAR.com, and NBA.com. Management thought that meant the staff had to know how to play sports.

Google MapsThe track where Armstrong and his coworkers would run laps

The company had a crappy office park headquarters far from Seattle's hip downtown. The only thing employees didn't hate about it was that it was right next to Bellevue Community College, which let Starwave employees use its athletic facilities.

So the staff was always training for something during lunch — 200 mile relays, ultimate Frisbee tournaments, whatever. In each sport, Armstrong was always the best.

"He's fast, he's strong, he can do it all," says a former colleague. "He's a golden boy in athletics. Anything you want him to do, he can do."

In 1997, Disney, which already owned ESPN, bought a controlling stake in Starwave and moved four employees to New York to work on an ABC News site and other projects. Armstrong, still in his early-mid-20s, was one of the four.

Coming to ABC's headquarters from Seattle, Armstrong was a huge underdog. The brand advertising sales world is still dominated by TV. The Internet was still a tiny experiment that didn't move the needle. And yet, Armstrong quickly made a name for himself in New York.

He did two things in particular that impressed colleagues. When Disney launched ABCNews.com in May 1997, Armstrong made himself the "point guy" for sales for the entire franchise. He stunned his bosses by selling a million-dollar package to health care company Columbia/HCA. That was a lot of money for Internet ads. Meanwhile, Armstrong became "the guy" doing cross-platform advertising sales for ESPN. To do that, Armstrong had to gain the trust of the ESPN TV sales guys who had the run of the place.

A former colleague remembers being amazed to see Armstrong had managed to get "into the club."

"He was the kid at the grownup table who just kept flirting with overstepping the natural bounds of things, but everyone liked him too much and let him get away with it. The ESPN sales guys then — they were TV sales guys — they’re the old, crusty pros. Remember, Tim was 26, 27. They let him into the club and it was pretty dramatic."

Suddenly, Armstrong was the guy at Disney who knew how to sell TV, plus Internet, plus magazine advertising to big brands.

Next, Armstrong joined a news-and-games startup called Snowball.com as vice president of sales and partnerships. Snowball eventually failed. But before it did, Armstrong got a call from a friend who told him that the head of revenue at a Mountain View-based startup called Google was coming to New York and had asked for an introduction.

Google MapsThe Starbucks where Armstrong hired early Google sales people

From $700,000 to $22 Billion

On the northwest corner of 86th Street and Columbus Avenue — the leafy heart of Manhattan's brownstone-rich Upper West Side — there is a red brick building. On the first floor there is a Starbucks with windows onto Columbus Avenue and 86th street.

If you were walking by those windows in the fall of 2000 or spring of 2001, you could have seen a tall man in a suit sitting across the table from another man or woman. Between them, there would have been too many coffees for two people.

The man in the suit would have been Tim Armstrong, interviewing a candidate for a position in Google's rapidly growing sales force.

The reason for all the coffees was that Armstrong had struck a deal with the baristas. If they let him use the Starbucks as a conference room, he'd buy way too much coffee.

This Starbucks was a convenient location for Armstrong because his apartment was at the same intersection. For a while, that apartment doubled as Google's first office outside of its home base in Mountain View.

Armstrong had joined Google under the assumption that he'd move to California in a year. He never did. Instead, he stayed in New York and hired more than a thousand people.

When Armstrong joined Google, the company's advertising revenue was $700,000 for the year. By the time Armstrong left Google in 2008, the company's revenue had grown to $22 billion.

Armstrong obviously doesn't deserve all the credit for that growth. One reason Google grew into such a huge business is that Google ads are the most perfect ads that ever existed. Consumers search for products, and the people who make those products pay Google to put ads next to the search results that come up. People in the industry look at those ads and say: How hard could it have been to sell those? They sell themselves. Also, Armstrong's people weren't the only ones selling Google ads. The reason Sheryl Sandberg is the chief operating officer of Facebook is that she made a name for herself at Google building a large team of recent college graduates who helped local businesses buy Google ads for themselves.

But even if Armstrong doesn't deserve all the credit for Google's mind-boggling revenue growth, he does deserve some credit. Any portion of $22 billion of revenue growth over eight years is a hell of a lot of revenue.

Armstrong's biggest early challenge at Google was explaining to ad buyers what, exactly, he was selling. New York ad buyers didn't really think about text ads back then. They were buying banners and "rich media." Worse, people also didn't know what Google was at the time. It was number 13 out of 13 search engines in traffic and tiny compared to Yahoo and AOL.

Meanwhile, the biggest fights Armstrong had to win in his early Google days weren't with ad buyers. These fights, he now says, were the "yelling matches at Google over ads and whether or not we were in the ads business."

One battle was over head count. When Google co-founders Larry Page and Sergey Brin hired Armstrong, they told him he could hire 30 people. Armstrong hired that many. Then, after a year, he told Page and Brin he needed to hire 300 more.

Another big win for Armstrong was a Google product that put Google ads on other companies' web sites. Along with a colleague named John Ferm, Armstrong came up with this idea. He hired an executive named Kurt Abrahamson to run the effort. Though much-evolved, this "network" business now accounts for billions of dollars of Google’s revenues.

By 2007, Armstrong's Internet career had taken him from a star sales kid to a trusted startup manager to a world-famous business executive. Steve Ballmer asked him to run Microsoft's online businesses. When Yahoo needed a new CEO in 2008, Tim Armstrong was considered.

At the same time, Armstrong was dealing with a big management problem inside Google — the kind of problem that he would later face in spades at the helm of AOL. Armstrong had hired lots of people very quickly. That hiring had helped Google to grow as fast as it did. But in the rush to hire fast, the sales organization in New York had become a mess.

Armstrong had implemented what's called a "matrix" or "cross-functional" structure — one where people have more than one boss and work on different projects. To grow much more, Armstrong realized, Google needed to re-organize its more-than one thousand sales people into a line-based reporting structure, where people worked in one group with one function and had one boss.

And yet, Armstrong was slow to make this change.

By then, Google had moved into an office the size of a city block in Chelsea.

In one meeting in that building, Armstrong brought up the needed reorganization and told his gathered lieutenants, "Guys, we cannot dither on this any longer! We have to make a decision!"

One of those lieutenants remembers sitting in that room looking at Tim lecturing his team about "dithering" and thinking, “Tim, we've all said there are pluses and minuses. Either way we're going to get some resistance. You need to make a call.”

"But he couldn't do it," this person says now. "He left for AOL before he ever made that call."

Today, this source offers a theory as to why. And this theory gets to the heart of what is hard for Tim Armstrong and why he took so long to make similarly hard decisions at AOL.

"That matrix organization had gotten, not so much bloated, but overly complex," the Google executive says. "And [Armstrong] wanted to simplify it. He knew deep down that it was the right thing to do, but he knew that there would be a lot of collateral damage in the course of doing that. And the ones who would get damaged were friends of his."

"He's a very loyal guy. He made a commitment to different parts of that matrix organization, and damn it, he's not going to let them down. And even though we brought in McKinsey and they told us to unravel it and Tim bought into it as the right strategy, he couldn't get himself to do that because it would have been a breach of his personal loyalties."

This was the first time Armstrong would struggle to make a call that he knew to be the right call because making the decision would force him to hurt lots of people who had believed in something he built from the ground up.

In March 2009, Tim Armstrong stood waiting for an elevator. He was on the 11th floor of the Time Warner Center on New York's Columbus Circle.

Moments earlier, he'd been sitting at a table with Time Warner CEO Jeff Bewkes in the private conference room in the back of Bewkes' office.

Bewkes had been a Time Warner executive before it became AOL Time Warner, and Bewkes had always opposed the merger. Now Bewkes was looking for a CEO to run AOL — possibly as a spun-off, publicly-traded company. Bewkes had asked Armstrong if he would take the job.

Armstrong was pretty sure he was going to tell Bewkes yes.

Though not yet 40, Armstrong was already sensing how short life was. He'd decided what remained of his life was his most valuable possession. Because of that, he didn't want to waste any more time at Google, where, as a non-engineer in a company run by engineers, he did not have any room left to grow.

He figured that running AOL would be very difficult — the company had been in a desperate tailspin for more than 7 years. But Armstrong also viewed AOL as an undervalued asset. It had a well-known brand, and though it was a top-5 company on the Internet, its valuation was far smaller than the top 4: Google, MSN, Yahoo, and Facebook. Closing that valuation gap even in the slightest would be a huge success.

Plus, AOL still had a very profitable Internet access business. Armstrong believed this business could provide the capital needed for the kind of big bets AOL would have to make to turn itself around. Armstrong already had a specific investment in mind — a local news startup he had co-founded called Patch. He'd already put some of his own money into Patch and made an old friend, Jon Brod, CEO of the company. Armstrong believed Patch could fill one of "the last white spaces on the Internet."

Finally, Armstrong was in a position to take a risk with his career. At 38, his Google stock had already made him worth hundreds of millions of dollars. That money would not go away if AOL didn't work out.

The elevator arrived. Armstrong stepped through the open doors. Later, he called Bewkes and took the job.

A new hope

When Time Warner announced Armstrong's hire on March 12, 2009, a wave of relief washed over AOL's employees. 2008 had been a horrible year for the company. So had 2007. And 2006. And 2005. Really, it was hard to remember what a good year felt like. It seemed like every Christmas season, there were layoffs.

The basic problem was that AOL had become a big, rich company because, in the 1990s, tens of millions of Americans had paid AOL $20 per month to get online. But then came broadband and there went the appeal of dial-up Internet access. Advertising dollars were supposed to replace those lost dollars, but by 2008, even that business was collapsing.

A former senior AOL executive remembers AOL prior to Armstrong as "an environment that felt very demoralized and somewhat abused, with the constant revolving door of leadership, at multiple levels not just at the CEO level, constant changes in strategy, and no apparent real plan for winning."

BIArmstrong's first rally in Dulles

Armstrong began his first day at AOL by touring the company's New York offices. Then he flew to Dulles, Va., where AOL was headquartered until 2008. He met with his senior managers. Then the whole group walked out to a big tent where thousands of AOL employees were gathered in front of a stage.

Armstrong got on stage. He took a microphone. He shouted: "Are you guys committed to putting America back online?”

"Don’t worry about Wall Street!"

"Don’t worry about the press!"

"Worry about building great products!”

The crowd shouted back in jubilation.

Finally, this was a CEO they could love.

Finally, this was a winner.

Armstrong's AOL

The day of AOL's spin-out

Armstrong spent his first 100 days at AOL touring the company's offices around the world and meeting with AOL's more than 8,000 employees.

At the end of his tour, Armstrong hosted a dramatic meeting at the Time Warner Center where he revealed his plan for the company. At the front of the room, there were two whiteboards turned away from the audience. On one, Armstrong said, were ideas that employees had for the future of the company. On the other, were Armstrong's ideas. He turned around the whiteboards. The ideas were the same.

AOL, Armstrong decided, would be a media company powered by technology. It would, like Time Warner, Disney, and other traditional media companies, own multiple beloved content brands for the platforms of the future.

Then, over the next two-and-a-half years, Tim Armstrong gradually but dramatically re-shaped AOL.

He arranged its spin-out from Time Warner. He hired a board of directors and orchestrated a massive employee buyout to reduce head count and cut costs. He re-designed the AOL.com home page. He also redesigned AOL's headquarters in New York to make it look more like Google's offices.

He sold off Bebo, an embarrassingly unpopular social network that the prior AOL administration had acquired for $850 million. He signed a lucrative search deal with Google.

He replaced his entire executive team, hiring former Google colleagues and other talented executives from big Web companies. He told them that AOL, spun out with a $3.15 billion market cap, would eventually be a $20 billion company.

Not surprisingly, Armstrong also made missteps, gaffes, and strange decisions that reminded people that he was a rookie CEO. For example, he arguably took too long to sharply reduce AOL's workforce, a mistake that led to a continuation of the rolling "death by a thousand cuts" layoffs that had so demoralized AOL's team over the prior decade. He also imported some management practices from Google that didn't even make sense at Google, much less at AOL.

For example, as Google's founders had in Google's early years, Armstrong insisted on approving every hire AOL made and also showed a bias for hiring only graduates of top universities. This practice ensured that Armstrong would be able to personally "vet" every new employee. But it also created a frustrating bottleneck and offended some of his senior team.

Once, during a regular Monday morning review with top executives, one of Armstrong's lieutenants, the west coast product boss Jason Shellen, asked Armstrong if he could hire his temporary assistant full-time.

Armstrong took a moment to review the assistant's resume. Then Armstrong looked up and spoke at the speaker phone, through which Shellen was connected to the room.

He said, "We're not hiring people from the Melting Pot."

Before temping with AOL for the prior three months, Shellen's assistant had been a hostess at a chain fondue restaurant called the Melting Pot.

Armstrong said, "Why don't you just hire a Stanford grad?" That's where Armstrong had hired his executive assistant from at Google, after all — Maureen Marques. By then, Marques had gone on to become a senior executive at AOL.

Shellen couldn't believe it. He said, "This is the most ridiculous thing I've ever heard." He liked his assistant, the former hostess from Melting Pot. She had done good work for three months. And she was cheap at $45,000 per year.

Armstrong said: "We're not hiring her." Shellen's career at AOL ended not long afterwards.

Eventually, after learning on the job, Armstrong ended this micro-management practice. Now he personally approves only hires of Senior Vice President and above.

When he took over AOL, Tim Armstrong faced a choice. He could strip the company down to nothing but its dial-up business and re-distribute its profits to shareholders until the whole thing dried up. Or he could take those dial-up profits and make a few big bets on businesses that might someday grow into new growth engines.

Armstrong hadn't quit Google to run an annuity.

During his first three years running AOL, Armstrong used the cash flow from AOL's rapidly declining, but still very profitable, dial-up business to make two huge bets.

He bought Huffington Post for $315 million. And he poured hundreds of millions into his local news startup, Patch.

The Huffington Post deal was splashier. In February 2011, Tim Armstrong and Arianna Huffington invited AllThingsD reporter Kara Swisher to the Super Bowl in Texas so she could interview them about the deal they had just completed. From an outside perspective, this deal and AOL's earlier, much smaller acquisition of tech news site TechCrunch, were Armstrong's first major financial commitments to building a multibrand media company — a new-age Disney.

But Armstrong had also come into AOL with a plan to spend hundreds of millions of dollars on a brand he believed would someday be as large as or larger than the Huffington Post: Patch.

Armstrong had come up with the idea for Patch on a Saturday morning in 2007. He was driving to his home in Riverside, Conn., with his kids in the car. At a stoplight, he spotted a bunch of signs stuck into the ground advertising stuff to do around town. At home, Armstrong checked and couldn't find an online calendar listing local events.

Armstrong called the editor of the local paper and told him he should build such a product into the paper's website.

The editors said, "We don't really need any help. We have a fine business."

Armstrong disagreed, and decided to start a company around local news and event listings for communities like his own. He called it Patch, and put Jon Brod in charge of it. Brod was a friend who had been running Armstrong's personal investment fund.

Google MapsArmstrong came up with Patch at a stoplight in Greenwich

When Time Warner asked Armstrong to run AOL in 2009, Armstrong said he would do it so long as Time Warner acquired Patch and gave it to AOL to run. Armstrong agreed to forgo any profits in the sale. Armstrong believed Patch would eventually be the growth engine that saved AOL. Time Warner agreed to Armstrong's request, and it bought Patch in the summer of 2009.

After AOL spun out of Time Warner to become a public company in late 2009, Armstrong had to convince the company's board of directors to allow him to invest heavily in Patch. This wasn't hard because Armstrong had, with the help of executive recruiter Jim Citrin, just hand-picked AOL's board of directors. Everyone joining the board already knew what they were getting into.

At one of his first board meetings, Armstrong told the assembled directors that Patch was "a huge opportunity," but that "it's not for the faint of heart." He promised to keep an eye on Patch metrics and report them. He wanted to make sure the board was comfortable with the big bet he planned to make. The board authorized him to invest $50 million in Patch during 2010. It allowed him to spend $160 million in 2011.

By some estimates, the board would eventually allow Armstrong to invest a staggering $500 million in Patch, exceeding AOL's purchase price in Huffington Post by almost $200 million.

This money went toward hiring people — lots of people. Armstrong gave Patch executives a simple direction: Blow this thing out. They did. By 2013, AOL would set up more than 800 Patch sites around the country. For a time, each site was operated by at least one editor. Hundreds more Patch employees sold ads. AOL chose locations for Patch sites using an algorithm that considered 59 variables from voter turnout to average income.

Patch, importantly, was Armstrong's baby. Patch had — and has — executives who believe in it, but they were there because Armstrong created the company and found a way to fund it.

"Patch was his," says a former AOL executive who reported directly to Armstrong. "In management meetings it wasn't, 'What do you think of Patch?' It was, 'Here's what we're doing with Patch."

One Monday morning during the fall of 2011, Armstrong sat down for his regular meeting with his senior executives in a conference room at AOL's headquarters called the 110% Room.

By then, Patch had already consumed more than $100 million. But that morning, Armstrong made a presentation to his lieutenants on plans to invest even more.

When he was done, Armstrong looked around at his gathered executives.

He said to them: "Anybody object?"

No one said anything.

And why would they?

He was their boss. And Patch was his.

But AOL wasn't his. AOL was AOL's shareholders'. And Tim Armstrong's lieutenants weren't the only ones concerned about all the AOL money Tim Armstrong was pouring into Patch.

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The Board Room

Editors' Picks

Why would you think that it's necessary or desired for the reader to come away from this piece thinking that what Armstrong did was "OK"? I don't get why you'd think that this is some loose goal of the article, at all.

Knowing the "why" regarding some actions or learning more about the context surrounding some act need not, in any way, excuse or justify anything. It just gives you a fuller picture of how the event unfolded. Human beings do bad, irrational, damnable things, for which there are no justifications--but there are always reasons. Some context or set of conditions motivated the individual to take the action. Your comment seems to say that discussing these reasons--looking for "why"--is useless or irrelevant unless it the information discovered actually "excuses" the person from acting as he/she did. That ain't gonna happen in the majority of cases, but knowing the context can yield valuable information, as I think it did here.

If your response is, "Yeah, but Armstrong is still wrong for what he did," you've missed my point completely.

It's not easy being at the top. In fact, leading people, companies is one of the hardest things you can do. The public, your staff don't see the pain, the heart that goes into it. They do see that moment you're under pressure and you snap. It's important as a leader to be building character, and practicing grace ever single day, so that you don't pay many times over for people mistakes--especially public ones, such as this one. Great article.

At the end of this captivating article I could not decide if I hated Tim Armstrong, admired him, or empathized with him. Perhaps all of the above. Which was possibly the intent and under lying theme of the story, and the man himself. Well done to the writers and editors of this piece.

Mr. Armstrong it would be best if you read the book "The one Minute manager" you may have had some good ideas and be successful but know this. You treat your staff and workers like they are nothing, then expect your precious AOL to suffer. Most importantly remember this Allah is watching you and angels are recording everything you do, so when the day of judgment comes you alone will answer for your deceit.

Were you paid to to damage control for this creep? Making excuses for such a horse's arse excuse for a a human being is laughable. Flippantly firing a coworker in front of 1000 employees is despicable behavior. Period. If you can write this well how can you not get this?

I figured this was going to be a pro-Armstrong propaganda fluff piece. First show him as corrupt as he is, then make excuses for that corruption.

There is no excuse for firing someone in front of others. None. This is bullying behavior, an attempt to show the people that he still has his manliness.

Not approving an assistant who proven herself because she worked in a restaurant he didn't approve of in the past, and didn't have a degree from an approved Ivy League university, shows this guy is shallow, and not results oriented.

There clearly is no meritocracy in AOL under Armstrong. None whatsoever. You want to work there? Gotta have an Ivy League degree, where spoiled rich kids with entitlement mentalities go. If you have a state university degree, live in the real world, and have a track record of doing great work, he does not care. Results do not matter. Just the correct "degree" does.

Writing this piece was a waste of time. He's not going to hire you, Mr. Cheerleader.